Vacation rentals in Leonardtown
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Top-rated vacation rentals in Leonardtown
Guests agree: these stays are highly rated for location, cleanliness, and more.
Guest suite in Lusby
4.99 out of 5 average rating, 299 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own completely private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is beautiful Solomon’s island. Boaters welcome!
Feb 25 – Mar 4
Cottage in Leonardtown
4.93 out of 5 average rating, 193 reviewsPotomac River Freedom Cottage
Welcome to the Freedom Cottage! We hope you will have a wonderful relaxing stay. Guest access will be provided via a keycode which will be emailed prior to arrival, spare key hanging inside. Guests will have access to the entire house and grounds (front and rear yard, stretching down to the beach/water). I won't be there for check-in/out but guests are encouraged to call/text during their stay if any questions arise. **Off-season long term rentals available, please contact me to discuss.
Apr 19 – 26
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 292 reviewsHistoric St.Mary's City at the Lazy Bear Cottage
Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.
Oct 13 – 20
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Leonardtown vacation rentals
Other great vacation rentals in Leonardtown
Guest suite in Colonial Beach
4.97 out of 5 average rating, 257 reviewsBayview Bungalow
Jun 9 – 16
Cabin in Lusby
4.91 out of 5 average rating, 203 reviewsPeaceful Waterfront Retreat on The Bay
Oct 22 – 29
Apartment in Lexington Park
4.93 out of 5 average rating, 187 reviewsPrivate apartment with kitchenette
Nov 16 – 23
Home in Lusby
5.0 out of 5 average rating, 110 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Oct 20 – 27
Home in Montross
4.92 out of 5 average rating, 144 reviewsTranquil River Home
Nov 17 – 24
Guest suite in Leonardtown
4.87 out of 5 average rating, 190 reviewsHappy Guesthouse! Located waterfront
Feb 12 – 19
Cottage in Saint Leonard
4.99 out of 5 average rating, 101 reviewsCaptain Jack's Bay Hideaway
Sep 3 – 10
Apartment in Leonardtown
4.94 out of 5 average rating, 33 reviewsRetreat at Fenwick
Sep 29 – Oct 6
Home in Leonardtown
4.95 out of 5 average rating, 39 reviewsOld Bay Inn
Sep 25 – Oct 2
Home in Leonardtown
5.0 out of 5 average rating, 19 reviewsWater's Edge Cottage | Luxury Retreat
Sep 18 – 25
Apartment in Leonardtown
4.92 out of 5 average rating, 13 reviewsBeech Creek Farm Apt
Apr 4 – 11
Home in Leonardtown
5.0 out of 5 average rating, 10 reviewsWaterfront Cottage w/ Incredible Views
May 19 – 26
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